Fatty-alcohols, particularly fatty-diols (or aliphatic diols) are amphipathic molecules having many commercial and industrial uses. For example, fatty alcohols find use as emollients and thickeners in cosmetics and foods and as industrial solvents, plasticizers, lubricants, emulsifiers, building blocks of polymers, etc., (see e.g., H. Maag (1984) Journal of the American Oil Chemists' Society 61(2): 259-267). Of particular usefulness are the 1,3-fatty-diols.
1,3-fatty-diols are useful as lubricants, as linking molecules between other molecules e.g., example in the production of polymers. 1,3-fatty diols are also useful as surfactants and as precursors to surfactants, for example, 1,3-fatty diols can be used to prepare “Gemini” surfactants in which both alcohol moieties are chemically modified (e.g., ethoxylated, glycosylated, sulfated, etc.). Gemini surfactants, or Gemini-like surfactants exhibit superior properties compared to those of analogous conventional surfactants (see, e.g., Gemini Surfactants: Synthesis, Interfacial and Solution-Phase Behavior, and Applications, Vol. 117, Zana, R.; Xia, J., Eds.; Marcel Dekker: New York, 2004).
The 3-hydroxy moiety of 1,3-fatty-diols forms a chiral center at the third carbon (C-3) which makes 1,3-fatty-diols useful as synthons for the production of chirally important compounds such as pharmaceuticals, nutraceuticals, pesticides, herbicides, flavors, fragrances, solvents, bioactive compounds, etc.
In addition to the functionality of the hydroxyl groups, variations in the structure of the carbon chain of 1,3-fatty diols provide molecules with additional chemistries and/or potentially new properties that can be used to address old problems in an improved way and/or which can find new uses altogether. For example, unsaturated fatty diols have additional functional groups in the form of double bonds which are available for chemical reactions.
Unsaturated fatty alcohols and fatty-diols are particularly valued because the presence of the double bond contributes a number of favorable properties on the molecule. For example, compared to their saturated counterparts, unsaturated fatty diols have lower melting point, higher solubility in water and offer the possibility of introducing functional groups into the C═C double bond (Egan, R., et al., (1984) Journal of the American Oil Chemists' Society, Vol. 61 (2): 324-329). Thus, unsaturated fatty alcohols are important intermediates for a large number of products of the chemical industry (see e.g., U. Ploog et al. in Seifen-Ole-Fette-Wachse 109, 225 (1983)).
Unlike saturated fatty-diols, which are readily produced from petroleum precursors using e.g., the Prins reaction (see e.g., E. Arundale, L. A. Mikeska Chem. Rev.; 1952; 51(3); 505-555) unsaturated fatty diols are much more difficult to produce from petrochemical materials and processes.
Typically, unsaturated fatty alcohols are produced by subjecting fatty acid methyl ester mixtures derived from oils such as e.g., sunflower, palm, palm kernel and coconut to high-pressure hydrogenation in the presence of chromium- and/or zinc-containing mixed oxide catalysts (see e.g., Ullmann's Encyclopedia of Industrial Chemistry 7th Edition, Vol. 14: 117. John Wiley and Sons, Inc. 2011). The zinc chromite type catalysts promote selective hydrogenation of the carbonyl group instead of the C═C double bond (see e.g., Adkins and Sauer, (1937) Journal of the American Chemical Society, Vol. 59 (1):1-3).
Unfortunately, because unsaturated fatty alcohols and unsaturated fatty-diols are produced only from limited numbers of natural oils, the supply of raw materials can be volatile and variable. Additionally, the reliance on natural oils and their inherent structures for the production of fatty diols limits the variety of chemical structures that can be produced.
Clearly then, since 1,3-fatty diols and especially, unsaturated 1,3-fatty-diols, are such useful molecules, what is needed in the art are new 1,3-fatty-diols.
Fortunately, as will be clear from the detailed description that follows, the present disclosure provides for this and other needs.